| August 6 | | |
| D Trevor Carrick | | D Kyle Wood |
| July 30 | | |
| F Ryan Callahan 2020 5th-round pick | | G Mike Condon 2020 6th-round pick |
| July 29 | | |
| F Nikita Gusev | | 2020 3rd-round pick 2021 2nd-round pick |
| July 26 | | |
| D John Marino | | 2021 6th-round pick* |
| July 25 | | |
| D Jordan Schmaltz | | D Andreas Borgman |
| July 23 | | |
| F David Clarkson 2020 4th-round pick | | G Garret Sparks |
| July 19 | | |
| F James Neal | | F Milan Lucic 2020 3rd-round pick* |
| July 16 | | |
| F Zack Smith | | F Artem Anisimov |
| July 9 | | |
| F Alexander Nylander | | D Henri Jokiharju |
| July 1 | | |
| F Jimmy Vesey | | 2021 3rd-round pick |
| D Nikita Zaitsev F Connor Brown F Michael Carcone | | D Cody Ceci D Ben Harpur F Aaron Luchuk 2020 3rd-round pick |
| June 30 | | |
| F Nicolas Deslauriers | | 2020 4th-round pick |
| F Andrew Shaw 2021 7th-round pick | | 2020 2nd-round pick 2020 7th-round pick 2021 3rd-round pick |
| G James Reimer | | G Scott Darling 2020 6th-round pick |
| June 29 | | |
| F Phil Kessel D Dane Birks 2021 4th-round pick | | F Alex Galchenyuk D Pierre-Olivier Joseph |
| D Jacob MacDonald | | F Dominic Toninato |
| June 28 | | |
| F Andre Burakovsky | | F Scott Kosmachuk 2020 2nd-round pick 2020 3rd-round pick |
| D Colin Miller | | 2021 2nd-round pick 2022 5th-round pick |
| June 27 | | |
| F Erik Haula | | F Nicolas Roy 2021 5th-round pick* |
| June 25 | | |
| F Carl Soderberg | | D Kevin Connauton 2020 3rd-round pick |
| June 24 | | |
| D Calvin de Haan F Aleksi Saarela | | G Anton Forsberg D Gustav Forsling |
| F Tyler Pitlick | | F Ryan Hartman |
| June 22 | | |
| No. 211 pick | | 2020 7th-round pick |
| No. 208 pick | | 2020 7th-round pick |
| No. 201 pick | | 2020 7th-round pick |
| No. 153 pick | | No. 211 pick 2020 7th-round pick |
| No. 143 pick | | No. 177 pick No. 191 pick |
| No. 136 pick | | 2020 5th-round pick |
| No. 108 pick | | 2020 4th-round pick |
| No. 102 pick | | No. 122 pick No. 175 pick |
| F Francis Perron No. 215 pick | | F Tom Pyatt No. 164 pick |
| No. 91 pick | | No. 118 pick No. 129 pick |
| No. 81 pick | | No. 104 pick No. 114 pick |
| No. 75 pick | | 2020 3rd-round pick |
| No. 74 pick | | No. 98 pick No. 151 pick No. 207 pick |
| No. 59 pick | | No. 73 pick No. 99 pick |
| No. 55 pick | | No. 82 pick No. 91 pick |
| No. 50 pick | | No. 64 pick No. 126 pick |
| No. 41 pick | | No. 48 pick No. 82 pick |
| F John Hayden | | F John Quenneville |
| F J.T. Miller | | G Marek Mazanec No. 71 pick 2020 1st-round pick* |
| No. 37 pick | | No. 44 pick No. 83 pick |
| No. 34 pick | | No. 45 pick No. 65 pick |
| D P.K. Subban | | D Steve Santini D Jeremy Davies 2019 2nd-round pick 2020 2nd-round pick |
| F Patrick Marleau 2020 1st-round pick* 2020 7th-round pick | | 2020 6th-round pick |
| June 21 | | |
| No. 11 pick | | No. 14 pick No. 45 pick |
| June 18 | | |
| D Justin Braun | | 2019 2nd-round pick 2020 3rd-round pick |
| June 17 | | |
| D Jacob Trouba | | D Neal Pionk 2019 1st-round pick |
| June 15 | | |
| D Olli Maatta | | F Dominik Kahun 2019 5th-round pick (TB) |
| June 14 | | |
| D Radko Gudas | | D Matt Niskanen |
| G Connor Ingram | | 2021 7th-round pick |
| June 3 | | |
| F Kevin Hayes | | 2019 5th-round pick |
| May 30 | | |
| 2019 7th-round pick* | | D Fedor Gordeev |
| Apr. 30 | | |
| D Adam Fox | | 2019 2nd-round pick 2020 3rd-round pick* |
| Feb. 25 | | |
| F Alex Broadhurst | | Future considerations |
| D Chris Wideman | | F Jean-Sebastien Dea |
| F Nic Petan | | F Par Lindholm |
| F Linus Karlsson | | F Jonathan Dahlen |
| D Bogdan Kiselevich | | 2021 7th-round pick |
| D Nathan Beaulieu | | 2019 6th-round pick |
| D Erik Gudbranson | | F Tanner Pearson |
| F Matt Hendricks | | 2020 7th-round pick |
| F Marcus Johansson | | 2019 2nd-round pick 2020 4th-round pick |
| F Wayne Simmonds | | F Ryan Hartman 2020 4th-round pick* |
| D Michael Del Zotto | | 2019 6th-round pick |
| F Mark Stone F Tobias Lindberg | | D Erik Brannstrom F Oscar Lindberg 2020 2nd-round pick (DAL) |
| F Mikael Granlund | | F Kevin Fiala |
| D Oscar Fantenberg | | 2020 4th-round pick* |
| D Adam McQuaid | | 2019 4th-round pick 2019 7th-round pick |
| F Derick Brassard 2020 6th-round pick* | | 2020 3rd-round pick |
| F Tomas Jurco | | Future considerations |
| F Cliff Pu | | Future considerations |
| F Jordan Weal | | F Michael Chaput |
| F Kevin Hayes | | F Brendan Lemieux 2019 1st-round pick 2022 4th-round pick* |
| G Keith Kinkaid | | 2022 5th-round pick |
| F Brian Gibbons | | D Patrick Sieloff |
| Feb. 24 | | |
| F Gustav Nyquist | | 2019 second-round pick* 2020 third-round pick* |
| D Brandon Montour | | F Brendan Guhle 2019 1st-round pick (SJ/STL) |
| F Spencer Watson | | F Matheson Iacopelli |
| F Nicholas Baptiste | | Future considerations |
| Feb. 23 | | |
| F Mats Zuccarello | | 2019 2nd-round pick* 2020 3rd-round pick* |
| F Ryan Dzingel 2019 7th-round pick (CGY) | | F Anthony Duclair 2020 2nd-round pick 2021 2nd-round pick |
| D Ben Lovejoy | | D Connor Carrick 2019 3rd-round pick |
| Feb. 22 | | |
| F Matt Duchene D Julius Bergman | | F Vitaly Abramov F Jonathan Davidsson 2019 1st-round pick 2020 1st-round pick* |
| D Nick Jensen 2019 5th-round pick (BUF) | | D Madison Bowey 2020 2nd-round pick |
| F Vincent Praplan | | Future considerations |
| Feb. 21 | | |
| F Carl Hagelin | | 2019 3rd-round pick 2020 6th-round pick* |
| Feb. 20 | | |
| F Charlie Coyle | | F Ryan Donato 2019 5th-round pick |
| Feb. 18 | | |
| F Peter Holland | | D Darren Raddysh |
| Feb. 16 | | |
| F Sam Gagner | | F Ryan Spooner |
| G Cam Talbot | | G Anthony Stolarz |
| Feb. 12 | | |
| G Marek Mazanec | | 2020 7th-round pick |
| Feb. 11 | | |
| D Blake Siebnaler | | 2019 7th-round pick* |
| F Nate Thompson 2019 5th-round pick | | 2019 4th-round pick |
| Feb. 9 | | |
| F Dale Weise D Christian Folin | | D David Schlemko F Byron Froese |
| Feb. 8 | | |
| F Emil Pettersson | | F Adam Helewka F Laurent Dauphin |
| Feb. 6 | | |
| F Cody McLeod | | 2020 7th-round pick |
| F Brian Boyle | | 2019 2nd-round pick |
| F Jean-Christophe Beaudin | | F Max McCormick |
| Feb. 1 | | |
| F Derick Brassard F Riley Sheahan 2019 2nd-round pick 2019 4th-round pick 2019 4th-round pick (MIN) | | F Nick Bjugstad F Jared McCann |
| Jan. 30 | | |
| D Michael Kapla | | D Ryan Murphy |
| Jan. 28 | | |
| D Jake Muzzin | | F Carl Grundstrom D Sean Durzi 2019 1st-round pick |
| D Jamie Oleksiak | | 2019 4th-round pick |
| Jan. 21 | | |
| D Brad Hunt 2019 6th-round pick | | 2019 5th-round pick* |
| Jan. 17 | | |
| F Taylor Leier | | F Justin Bailey |
| F Nino Niederreiter | | F Victor Rask |
| F Derek Grant | | F Joseph Blandisi |
| D Michael Del Zotto | | D Luke Schenn 2020 7th-round pick |
| Jan. 16 | | |
| F Pontus Aberg | | F Justin Kloos |
| Jan. 14 | | |
| F Connor Brickley | | F Cole Schneider |
| F Andrew Cogliano | | F Devin Shore |
| Jan. 11 | | |
| D Slater Koekkoek 2019 5th-round pick | | D Jan Rutta 2019 7th-round pick |
| F Jordan Weal | | 2019 6th-round pick |
| D Cody Goloubef | | F Paul Carey |
| F Morgan Klimchuk | | F Gabriel Gagne |
| Jan. 3 | | |
| D Jimmy Oligny | | Future considerations |
| G Jared Coreau | | Future considerations |
| Jan. 2 | | |
| G Anders Nilsson F Darren Archibald | | G Mike McKenna F Tom Pyatt 2019 6th-round pick |
| Dec. 30 | | |
| D Brandon Manning D Robin Norelli | | F Drake Caggiula D Jason Garrison |
| D Alex Petrovic | | D Chris Wideman 2019 3rd-round pick* |
| Dec. 29 | | |
| G Michael Hutchinson | | 2020 5th-round pick |
| Dec. 28 | | |
| F Giovanni Fiore | | D Trevor Murphy |
| Dec. 10 | | |
| D Steve Oleksy | | F Adam Cracknell |
| Dec. 5 | | |
| D Stefan Elliott F Tobias Lindberg | | D Macoy Erkamps F Ben Sexton |
| Dec. 3 | | |
| F Daniel Sprong | | D Marcus Pettersson |
| F Josh Leivo | | F Michael Carcone |
| Nov. 27 | | |
| F Morgan Klimchuk | | D Andrew Nielsen |
| Nov. 25 | | |
| F Nick Schmaltz | | F Dylan Strome F Brendan Perlini |
| Nov. 22 | | |
| D Chris Wideman | | 2020 6th-round pick |
| Nov. 21 | | |
| F Pavel Jenys | | D Stepan Falkovsky |
| Nov. 16 | | |
| F Ryan Strome | | F Ryan Spooner |
| Nov. 14 | | |
| F Tanner Pearson | | F Carl Hagelin |
| Nov. 10 | | |
| D Taylor Fedun | | 2020 7th-round pick* |
| Oct. 18 | | |
| F Mitch Hults | | Future considerations |
| Oct. 3 | | |
| D Gustav Olofsson | | F William Bitten |
| Oct. 1 | | |
| D Jack Dougherty | | F Nicholas Baptiste |
| D Brett Kulak | | D Matt Taormina D Rinat Valiev |
| D Connor Carrick | | 2019 7th-round pick* |
| Sept. 13 | | |
| D Erik Karlsson F Francis Perron | | F Josh Norris F Chris Tierney F Rudolfs Balcers D Dylan DeMelo 2020 1st-round pick* 2019 2nd-round pick* 2021 2nd-round pick* |
| Sept. 11 | | |
| D Adam McQuaid | | D Steven Kampfer 2019 4th-round pick 2019 7th-round pick* |
| Sept. 10 | | |
| F Max Pacioretty | | F Tomas Tatar F Nick Suzuki 2019 2nd-round pick |